Anthraquinon compound and process of making same.



MAX HENRY ISLER, 0F MANNHEIM, GERMANY, ASSIGNOR To BADISCHE,

ANILIN. 8: SODA FABRIK, OF LUDWIGSHAFEN-ON-IHE- RHINE, GER- MANY, A CORPORATION.

ANTHRAQUINON COMPOUND AND PROCESS OF MAKING SAME.

Specification of Letters Patent.

Patented March 6, 1906.

, A htaion filed October 31,1905. Serial No. 285,319.

To all whom it .may concern:

Be it known that I, MAX HENRY IsLEn, chemist, a citizen of the Swiss Republic, residing at Mannheim, in theGrand Duchy of Baden, German Empire, have invented new and useful Improvements in Anthraquinon Compounds and Processes of Making the Same, of which the followingis a specifica ms 1 l i r vyv I O I I v this being this first representative-of a new class of anthra uiilon compounds. The same new compoun can be obtained by condensing 2-amidoanthraquinon wi-th 1-chloranthra uinon,- although the reaction in this case oes not proceed so favorably. This dianthraquinonylamin consists of crystals which possess a metallic luster and which dissolve in concentrated sulfuric acid, yielding a greenish-blue solution. I prefer to carry out the reaction in the presence of a diluting My invention is not restricted to the use of the above-named compounds, since a similar condensation takes place if instead of I-chloranthraquinon the compound 1 amido 4- halogen-anthraquinon be condensed with 1- {amido-anthraqriinon, provided the amido group of the amidoehalogenanthraquinon be protected against reaction b T being previously converted into its acidy derivativefor example, into the acetyl derivative. After the condensation has taken lace the acetyl group can be easily split 0 '-for instance, by suitable treatment with sulfuric 6o acid -and the amido compound of the afore mentioned dianthraquinon larmn be obtainecl. Of course instead 0 the above-mentioned' halogen anthraquinons amido anthraquinons and halogen amido anthra quinons, their homologues and derivatives can be employed. Thus, for instance, by condensing together 1-acetyl-amido-Z-rnethylk chlor-anthraquinon and 1-amido-2-methylanthraquinon and by saponifying the reaction product the new compound amido-dimethyl dianthraquinonylamin can be obtained.

All the compounds of this new class which I have obtained are crystalline and are difii- '75 cultly soluble in most of the ordinary solvents, but are soluble in concentrated sul: furic acid. They are also sufficiently soluble in anilin and in nitrobenzene to enable them to be recrystallized from these solvents. On being treated with sulfonating agents-for in stance, with amixture' of fuming sulfuric acid and boric acid-they are converted into coloring-matters which dye wool from an acid bath shades which are very fast against the action of light and washing.

, The following examples will serve to fur-l ther illustrate the nature of my invention and the method of carrying it into practical effect; but my invention is not confined to these examples; The parts are by weight.

Example 1: Boil together for about fifteen (15) hours twenty-four (24) parts of-Z-chloranthraquinon, twenty-seven (27) parts of 1- amido-anthraquinon, one thousand (1,000) parts of naphthalene, twenty-five (25) parts of anhydrous sodium acetate, and five (5) T parts of copper chlorid. Allow the mixture to cool and then remove the naphthalene by boiling with toluene, whereupon the draw rco thraquinonylamin remains in the form of crystals, with a metallic luster. These are soluble in concentrated sulfuric acid, yielding a greenish-blue solution. They are diflicultly soluble in most solvents; but they can be recrystallized from nitrobenzene or from anilin. This 'dianthraquinonylamin can be converted into coloring-matter by heating it with fumtime. Filter Off the condensation product with 20 the aid of the pump and then wash with nitrobenzene, then with alcohol, then with dilute hydrochloric acid, and, finally, again with alcohol. In order to purify the product still further, it may be recrystallized from nitroben- '15 zene. From the product so obtained the acetyl grou mayeasl'ly be split off by dissolving the pro not in ten (10) times its weight of sulfuric acid containing about ninety-eight (98) per cent. of E 80 and then precipitatgo ing slowly with water, whereupon the reaction mixture becomes hot and the base separates out in a crystalline form. Upon recrystallization from nitrobenzene this base can be obtained in the form of dark-"blue needles,

3 5 with a metallic luster.

Exainple'3: Boil together for two (2) hours i one hundred and fifty (150) parts of nitrobenzene, ten parts of 1-mono-acet,amido- 2 -methyl 4 chlor anthraquinon, ten (10) 0 parts of l-amido 2 7 methyl-4-para toluidoanthraquinon, ten (10) parts of anhydrous sodium acetate, and two (2) parts of cuprous chlorid and work up the melt in the manner described in the foregoing Example 2.

5 y In the foregoing Examples 2 and 3 instead of 1mono-acetamido2-methyl 4 chlor 'anthraquinon other acidyl derivatives of 1- amid0-2-methyl-4-chlor-anthraquinon or the acidyl derivatives of other 1a1nido-4-chlor- 5o anthraquinonssuch, for example, as 1.5-

ing sulfuric acid, with or without the addition 2. The process for the production of dianthraquinonylamin by heating 1'amidoan thraquinon with 2-chlor-anthraquinon in the presence of a condensing agent.

3. The process for the production of dianthraquinonylamin by heating l -amido-an- 7o thraquinon with Z-chlor-anthra uinon in the presence of copper chloridand so 'um acetate.

4. As new articles of manufacture dia'nthraquinonylamin compounds which are crystalline and diflieultly soluble in most of the ordinary solvents, fairly soluble in anilin and nitrobenzene and soluble in concentrated sul' furic acid and which on being 'sulfonated yield coloring-matters which dye wool from anacid-bath.

5. As a new article of manufacture dianthraquinonylamin which can be obtained from 1-amido-anthraquinon and 2-chlor-anthraquinon, which new compound is crystalline with a metallic luster and diflicultly soluble in most of the ordinary solvents, fairly soluble in anilin and nitrobenzene and soluble in concentrated sulfuric acid yielding a; greenish-blue solution and which on being sulfonated yields a coloring-matter which dyes wool from an acid-bath brownish-red shades.

In testimony whereof I have. hereunto set my hand in the presence of two subscribing witnesses.

MAX HENRY ISLER!v I Witnesses: I I

J. Auto. LLOYD, Jos. H. LEUTE. 

